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Optimized Synthesis of New N-Mustards Based on 2-Mercaptobenzoxazole Derivatives with Antitumor Activity
New di-(β-chloroethyl)-amides of some acids derived from 2-mercaptobenzoxazole were prepared by reaction of the corresponding pivalic mixed anhydrides with di-(β-chloroethyl)-amine. A study regarding the optimization of the chemical reactions was made for the case of di-(β-chloroethyl)-amines. The q...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8145375/ https://www.ncbi.nlm.nih.gov/pubmed/33926050 http://dx.doi.org/10.3390/biomedicines9050476 |
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author | Cheptea, Corina Sunel, Valeriu Morosanu, Ana Cezarina Dimitriu, Dan Gheorghe Dulcescu-Oprea, Mihaela Maria Angheluta, Mihai-Daniel Miron, Mihaela Nechifor, Cristina Delia Dorohoi, Dana Ortansa Malancus, Razvan Nicolae |
author_facet | Cheptea, Corina Sunel, Valeriu Morosanu, Ana Cezarina Dimitriu, Dan Gheorghe Dulcescu-Oprea, Mihaela Maria Angheluta, Mihai-Daniel Miron, Mihaela Nechifor, Cristina Delia Dorohoi, Dana Ortansa Malancus, Razvan Nicolae |
author_sort | Cheptea, Corina |
collection | PubMed |
description | New di-(β-chloroethyl)-amides of some acids derived from 2-mercaptobenzoxazole were prepared by reaction of the corresponding pivalic mixed anhydrides with di-(β-chloroethyl)-amine. A study regarding the optimization of the chemical reactions was made for the case of di-(β-chloroethyl)-amines. The quantum chemical analysis by Spartan’14 was made in order to establish the most stable configuration of the ground electronic states for the obtained chemical structures and some physico-chemical parameters of N-mustards reported in this paper. Mercaptobenzoxazoles substituted in the side chain with the cytotoxic group show antitumor activity and they inhibit Ehrlich Ascites in an appreciable proportion compared to the drug I.O.B.-82, as our studies evidenced. |
format | Online Article Text |
id | pubmed-8145375 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-81453752021-05-26 Optimized Synthesis of New N-Mustards Based on 2-Mercaptobenzoxazole Derivatives with Antitumor Activity Cheptea, Corina Sunel, Valeriu Morosanu, Ana Cezarina Dimitriu, Dan Gheorghe Dulcescu-Oprea, Mihaela Maria Angheluta, Mihai-Daniel Miron, Mihaela Nechifor, Cristina Delia Dorohoi, Dana Ortansa Malancus, Razvan Nicolae Biomedicines Article New di-(β-chloroethyl)-amides of some acids derived from 2-mercaptobenzoxazole were prepared by reaction of the corresponding pivalic mixed anhydrides with di-(β-chloroethyl)-amine. A study regarding the optimization of the chemical reactions was made for the case of di-(β-chloroethyl)-amines. The quantum chemical analysis by Spartan’14 was made in order to establish the most stable configuration of the ground electronic states for the obtained chemical structures and some physico-chemical parameters of N-mustards reported in this paper. Mercaptobenzoxazoles substituted in the side chain with the cytotoxic group show antitumor activity and they inhibit Ehrlich Ascites in an appreciable proportion compared to the drug I.O.B.-82, as our studies evidenced. MDPI 2021-04-26 /pmc/articles/PMC8145375/ /pubmed/33926050 http://dx.doi.org/10.3390/biomedicines9050476 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Cheptea, Corina Sunel, Valeriu Morosanu, Ana Cezarina Dimitriu, Dan Gheorghe Dulcescu-Oprea, Mihaela Maria Angheluta, Mihai-Daniel Miron, Mihaela Nechifor, Cristina Delia Dorohoi, Dana Ortansa Malancus, Razvan Nicolae Optimized Synthesis of New N-Mustards Based on 2-Mercaptobenzoxazole Derivatives with Antitumor Activity |
title | Optimized Synthesis of New N-Mustards Based on 2-Mercaptobenzoxazole Derivatives with Antitumor Activity |
title_full | Optimized Synthesis of New N-Mustards Based on 2-Mercaptobenzoxazole Derivatives with Antitumor Activity |
title_fullStr | Optimized Synthesis of New N-Mustards Based on 2-Mercaptobenzoxazole Derivatives with Antitumor Activity |
title_full_unstemmed | Optimized Synthesis of New N-Mustards Based on 2-Mercaptobenzoxazole Derivatives with Antitumor Activity |
title_short | Optimized Synthesis of New N-Mustards Based on 2-Mercaptobenzoxazole Derivatives with Antitumor Activity |
title_sort | optimized synthesis of new n-mustards based on 2-mercaptobenzoxazole derivatives with antitumor activity |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8145375/ https://www.ncbi.nlm.nih.gov/pubmed/33926050 http://dx.doi.org/10.3390/biomedicines9050476 |
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